Category: 107263-95-6

Umemoto, Teruo published the artcileHighly Selective Fluorinating Agents: a Counteranion-Bound N-Fluoropyridinium Salt System, COA of Formula: C6H5F4NO3S, the publication is Journal of Organic Chemistry (1995), 60(20), 6563-70, database is CAplus.

A series of alkyl- or (trifluoromethyl)-substituted N-fluoropyridinium 2-sulfonates 2a-h, differing in fluorinating power, were synthesized, and assessment was made of the effectiveness of each selective fluorinating agent. N-Fluoropyridinium 3- and 4-sulfonates were also synthesized. Power-variables 2a-h were found to be highly selective fluorinating agents for a wide range of nucleophilic substrates such as activated aromatics, enol trialkylsilyl and alkyl ethers, active methylene compounds, activated olefins, and sulfides. This regioselectivity increased with the bulkiness of the silyl part, and with the most bulky triisopropylsilyl group exclusive 6-fluorination was achieved. Preferential β-stereoselective fluorination at the 6-position was observed N-Fluoropyridinium 2-sulfonates were activated with an acid. This acid-catalyzed fluorination led to the preferential p-fluorination of anisole. The present results can be explained based on the capacity of the 2-sulfonate anion to interact with the hydroxy group of phenol or naphthol, NH group of phenylurethane, silicon atoms of silyl ethers, or protons of acids.

Journal of Organic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C12H9NO, COA of Formula: C6H5F4NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Ueno, Tetsuya published the artcileSynthesis and properties of fluoroazulenes. II. Electrophilic fluorination of azulenes with N-fluoro reagents, Name: 1-Fluoropyridiniumtriflate, the publication is Bulletin of the Chemical Society of Japan (1996), 69(6), 1645-1656, database is CAplus.

1-Fluoro- and 1,3-difluoroazulenes were synthesized for the first time by the electrophilic fluorination of azulenes with N-fluoro reagents. Selective preparation of 1-fluoroazulenes were performed by the fluorination of Me azulene-1-carboxylates, followed by demethoxycarbonylation in 100% H₃PO₄. 2-Substituted azulenes were fluorinated in higher yields. In the ¹H NMR of 1-fluoroazulene, long-range J_FH values were not observed at H-2 and H-8, in contrast to those for 1-fluoronaphthalene. The 1-fluorine atom causes significant bathochromic shifts in the visible absorption of azulene, due to the so-called +Iπ effect.

Bulletin of the Chemical Society of Japan published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C13H14N2O, Name: 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Ueno, Tetsuya published the artcilesynthesis of 1-fluoro- and 1,3-difluoroazulenes, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is Chemistry Letters (1995), 169-70, database is CAplus.

Title compounds were synthesized by the reaction of azulene with N-fluoropyridinium salts in MeCN. Me azulene-1-carboxylates were also fluorinated to give the corresponding 3-fluoro derivatives On the basis of the UV-visible absorption spectra, the fluorine atom acts as an electron-donating group to the azulene π-system due to the +Iπ effect. A solution of azulene and N-fluoro-2,4,6-trimethylpyridinium triflate in MeCN were refluxed to give 1-fluoroazulene and 1,3-difluoroazulene. The yields of these 2 compounds decreased with more powerful fluorinating agents.

Chemistry Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C19H17N2NaO4S, Recommanded Product: 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileN-Fluoropyridinium triflate and its analogs. The first stable 1:1 salts of pyridine nucleus and halogen atom, Application In Synthesis of 107263-95-6, the publication is Tetrahedron Letters (1986), 27(28), 3271-4, database is CAplus.

N-Fluoropyridinium salts having non-nucleophilic counter-anions, e.g., I (R = F, R¹-R⁵ = H; R = F, R¹ = Me, R²-R⁵ = H; X = CF₃SO₃), and their derivatives were synthesized by treating pyridine-F₂ adducts with strong Broensted acids, their salts, or trimethylsilyl esters, or Lewis acids, or by allowing F₂ to react with N-trimethylsilylpyridinium salts I (R = SiMe₃).

Tetrahedron Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C7H7IN2O, Application In Synthesis of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileN-Fluoropyridinium triflate: an electrophilic fluorinating agent, Safety of 1-Fluoropyridiniumtriflate, the publication is Organic Syntheses (1990), 129-43, database is CAplus.

The title compound (I) was prepared by fluorination of pyridine with F₂ in MeCN in the presence of CF₃SO₃Na. Treating methoxy(trimethylsiloxy)estratetraene II with I in CHCl₂ gave 66% the 16α-fluoroestrone III. A variety of examples of the use of I and its derivatives are also described.

Organic Syntheses published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C10H12F6N4O6PdS2, Safety of 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileNovel base-initiated reactions of N-substituted pyridinium salts, COA of Formula: C6H5F4NO3S, the publication is Journal of Fluorine Chemistry (1996), 77(2), 161-168, database is CAplus.

Reaction of N-fluoropyridinium triflate with a base in dichloromethane gave 2-chloropyridine as the major product along with 2-pyridyl triflate and 2-fluoropyridine, regardless of the nature of the base. This base-initiated reaction was also shown to take place similarly in other halogenated alkanes, ethers, a nitrile, aromatics, a ketone, vinyl ethers, alcs. and trimethylsilyl acetate as solvents to give pyridine derivatives substituted with a solvent mol.(s) at the 2-position. N-(Trifluoromethanesulfonyloxy)- and (benzenesulfonyloxy)pyridinium salts were found to undergo the same base-initiated reaction. These reactions may be explained by a postulated singlet carbene produced through proton abstraction of N-substituted pyridinium salts. A similar carbene reaction may thus likely occur in the thermal decomposition of thiatriazole. The ab initio MO calculations revealed the structure and properties of the labile deprotonated N-fluoropyridinium cation and supported the carbene intermediate reaction mechanism rather than a pyridynium or pyridyl cation mechanism. Quarroz’s reports on the reactions of picolinic acid N-oxide and the reported reactions of pyridines with F₂, CH₃COOF or CsSO₄F in solvents may be explained by this carbene mechanism.

Journal of Fluorine Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C9H21NO3, COA of Formula: C6H5F4NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileα-Fluorination of sulfides with N-fluoropyridinium triflates, HPLC of Formula: 107263-95-6, the publication is Bulletin of the Chemical Society of Japan (1986), 59(11), 3625-9, database is CAplus.

The reaction of RSCH₂R¹ [I R = Ph, PhCH₂, C₆H₄Cl-4, Me, dodecyl; R¹ = H, CO₂Et, CO₂Me, CH₂CH(CO₂Me)NHCOCF₃] with N-fluoropyridium salts II (X = CF₃SO₃, BF₄), III, and IV was examined While the fluorinating power increased in the order of II (X = CF₃SO₃) < III < IV, the yield of α-fluoro sulfide decreased in the order of II > III, and IV no longer produced the α-fluoro sulfide. II (X = CF₃SO₃) was more reactive than II (X = BF₄). Thus, RSCHFR¹ were prepared by α-fluorination of I with II (X = CF₃SO₃) under mild conditions. RS(O)_nCHFR¹ (n = 1, 2) were easily prepared by α-fluorination of I with II, followed by oxidation

Bulletin of the Chemical Society of Japan published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C8H15ClN2, HPLC of Formula: 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Fujisawa, Hidehito published the artcileSimple procedure for preparation of α-fluoro esters by fluorination of ester enol silyl ethers with perchloryl fluoride, Application In Synthesis of 107263-95-6, the publication is Journal of Fluorine Chemistry (2002), 117(2), 173-176, database is CAplus.

A practical method for general preparation of α-fluoro esters by fluorination of the corresponding enol silyl ethers using diluted FClO₃ in the presence of suitable amount of amine is described. Fluorination of ester enol silyl ethers in THF at room temperature using diluted perchloryl fluoride (FClO₃) in the presence of ca. 0.5 M eq. of t-BuNH₂ as an additive produced the corresponding α-fluoro esters in over 80% yields. For example, fluorination of [(1-ethoxy-2-phenylethenyl)oxy]trimethylsilane with perchloryl fluoride gave α-fluorobenzeneacetic acid Et ester.

Journal of Fluorine Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Application In Synthesis of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yokoyama, Yasuo published the artcileThe development of a novel synthetic method for cyanofluoroamides using a cobaltadithiolene complex, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is Synthesis (2004), 701-705, database is CAplus.

N,N-Di-Et 2-cyano-2-fluoro-2-(phenylthio)acetamide reacted with germyl anion species to give the corresponding enolate. When this enolate was treated with an unsaturated organic halide, in the presence of a catalytic amount of cobaltadithiolene I, II was obtained in good yield. Interestingly, in the absence of I, no target product was obtained. This reaction proceeded smoothly under mild reaction conditions and only cyanofluoroamide was obtained.

Synthesis published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C17H14F3N3O2S, Recommanded Product: 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Kiselyov, Alexander S. published the artcileA novel synthesis of 2-substituted pyrido[1,2-a]-1,3,5-triazin-4-ones by the reaction of N-fluoropyridinium salts with cyanate ion and carbonitriles: evidence in support of a carbene intermediate, Product Details of C6H5F4NO3S, the publication is Tetrahedron Letters (1994), 35(2), 207-10, database is CAplus.

A carbene intermediate derived from N-fluoropyridinium cation is suggested in the novel synthesis of pyridotriazines I (R¹ = Pr, CMe₃, Ph) by the reaction of N-fluoropyridinium salts with cyanate ion and R¹CN.

Tetrahedron Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Product Details of C6H5F4NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem